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  • Highly enantioselective and recyclable organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in aqueous media.

Highly enantioselective and recyclable organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in aqueous media.

Organic & biomolecular chemistry (2012-09-15)
Subrata K Ghosh, Kritanjali Dhungana, Allan D Headley, Bukuo Ni
ABSTRACT

A new type of pyrrolidine-based organocatalyst, which was developed earlier in our lab, has been found to be very effective for the Michael addition reaction in aqueous solvents involving a wide range of α,β-unsaturated aldehydes and malonate derivatives. For the reactions studied, good to excellent yields (73%-96%) and high to excellent enantioselectivities (up to 97%) were obtained using this catalyst. In addition, the catalyst could be recycled up to four times with gradual reductions in yields and enantioselectivity observed after the second cycle.

MATERIALS
Product Number
Brand
Product Description

Supelco
Malonic acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Sigma-Aldrich
Pyrrolidine, ≥99.5%, purified by redistillation
Sigma-Aldrich
Malonic acid, ReagentPlus®, 99%
Sigma-Aldrich
Pyrrolidine, ≥99.0%
Sigma-Aldrich
Pyrrolidine, FG
Sigma-Aldrich
Pyrrolidine, 99%
Sigma-Aldrich
Sodium malonate dibasic, ≥97.0% (NT)